I for one, would like you to take a moment and describe what a 'day out on the town' means to you. In other words, would you provide a description of places you might go to or people you may see on a typical days outing.
The reason I ask is that your clothing should be selected to be appropriate to the people, places and occasions that you may encounter.
Jointly, I would also ask that you provide some photos of your existing clothes. For example, lay out all your dress shoes (then boots, then sneakers, etc) in a row in the floor and take a photo and tell us the make of each pair. Then, lay out your dress shirts on your freshly made bed, snap a photo. Do the same for yor coats, ties, socks, pants, belts, etc. Also state your budget or the most you are willing to spend.
I am aware that this is asking you to do some work in preparing these photos, but the more information we have about you, your lifestyle and your existing wardrobe, the better we will be able to make suggestions for you that will save you both time and money and also get you to where you want to be. Welcome to Styleforum will1356.